The squatter of Silicon Valley

Those workaholics who claim to live at their office have nothing on Eric Simons.

The 20-year-old is the founder of ClassConnect – an online platform that allows educators to build, share and collaborate on their lesson plans with other teachers around the world – and it had one of the biggest launches in Silicon Valley last year. He’s also the guy who spent five months squatting in AOL’s Palo Alto campus.

“In the first month, when I launched in March, I had 8,000 teachers and 50,000 students and parents using the thing. Then, by the end of the school year, we had doubled both those numbers,” says Simons.

He also managed to secure $50,000 in seed funding from Silicon Valley venture capitalist Paul Scherer and Clint Korver, co-founder of Ulu Ventures, a company which invests in early-stage internet-enabled consumer and business services. Both are also advisors to the company and their money allowed Simons to expand his team to five people and rent an apartment in Palo Alto.

Quite an accomplishment, especially for someone who only five months before found himself broke, homeless and abandoned by his business partners. He was so desperate, he started secretly living at the AOL Campus in Palo Alto, California, unable to give up the ClassConnect dream and determined to make his failing idea profitable.

“Any sane person would’ve quit,” says Simons. “But, I cared a lot about what we were trying to do and that’s why I made the decision, ‘I’m just going to figure out how to stay alive for the next few months, so I can get this thing online. It was a crazy bet, considering it was just me doing the marketing, doing the engineering, doing everything, but somehow I ended up pulling it off.”

However, Simons situation didn’t start out quite so desperate. Simons and his original partners were trying to do was improve the state of education in America and they were invited to Imagine K-12, an educational technology startup incubator on the AOL Campus, and given $20.000 to start trying. Things were looking up, until they started looking for a solution in all the wrong places.

Time was running out, the incubator only ran from June to September and after working so hard all summer with nothing to show for it, his partners decided to bail and go back to college because, in their words, “Running a start-up sucked.” However, Simons wasn’t about to give up that easily. He poured over the data and noticed there was a feature of their social network for educators that teachers actually were using in great numbers. It was the collaborative lesson planning component – the backbone of what would later become ClassConnect.

“Basically, I made a bet with myself,” says Simons. “I said, ‘If I focus entirely on this lesson planning piece, when I do launch this thing I bet I’ll have one of the best launches any educational technology company has ever had.”

But before he could pop champagne, he needed to get there and if he was going to get there, he needed a place to sleep. He’d already blown through their $20,000 in venture capital just trying to live in Silicon Valley over the summer. With no money, he eventually lost the team’s apartment and with no product, there was nothing to raise more capital with. The one thing he had to his name was a working security card that gave him access to the AOL grounds.

“I was already working there all day long and then just sleeping at our apartment, so when we lost the apartment I went back to AOL the next day. I was working there, it got to be night time and I was like, you know what? I’ll just sleep here. It wasn’t something I planned out. It was just, I’ll do this. I was spending all my time there anyway.”

Soon, one night turned into a few weeks and a few weeks turned into four months of squatting, largely unnoticed, on the third flour of the AOL building.

“I’d stay in touch with some of my buddies and was like, ‘Hey, could I crash at your place?’ and everyone was pretty much full. They were like, ‘Yeah sorry, I don’t have a spot right now, but in two weeks or a month I might.’ I needed a place to live and I realized I could probably make this work. There was everything I needed at this building: there was food, there were couches, they had a gym, so there were showers. I started doing it and at first it was definitely a temporary thing, but over time I was getting away with it and no one really noticed.”

Technically, he had every right to be there. Between the departure of 2011’s summer cohort and the arrival of the new one in January 2012, Imagine K12 gave former participants full access of the AOL Campus to work on their businesses. However, Simons’ use of that privilege was probably not what the organizers had in mind.

“As far as sleeping in general, I would pick a place that was way the hell out of the way that people wouldn’t go to. They had these offices with couches in them, so I would just grab those, close the door and turn off the lights. So, if anyone came in, they wouldn’t be able to get in because the door’s locked and if security tried to open the door, that gave me enough time to sit up and get my laptop out.”

Simons says he didn’t have a lot of clothes to begin with, so his entire wardrobe fit in a dufflebag, while he stored other clothes and valuables in the change room lockers near the gym. Food was also surprisingly easy to come by. Someone was always ordering-in for their department and they would always leave the leftovers for anyone who wanted them, so Simons would just saddle up to the makeshift buffet, fill three or four plates, eat one and save the rest in the lunchroom fridges for later.

All in all, it was a pretty sweet arrangement. He did have a few late-night close calls with security, but his laptop always provided the perfect cover: “I was just like, ‘Hey, how’s it going?’ and they’d respond, ‘Good. Up working late?’ and I’d be like, ‘Yeah, got to push some code out.” Incredibly, he was able to avoid detection for four months — with workers thinking he was always the last to leave and first to arrive – before, inevitably, shit hit the fan:

“I think this guy had been tracking me down for a few weeks,” says Simons. “I think someone had told him that someone was living out of there, so he just ripped the door open and started yelling at me. I was like, ‘Yeah, I don’t know what you’re mad about. I have my I.D.’ I was trying to play it down like it was not a big deal, but he wasn’t having it. Still, he couldn’t kick me out because I had my I.D. He was just yelling at me saying, ‘This isn’t a dorm! You can’t be sleeping here!”

The guy turned out to be the building manager and he’d caught Simons red-handed at 7 a.m. sleeping under a solar blanket without even missing a beat. Right on cue, he sent an angry e-mail to Imagine K12 and Simons’ show was over. “They were doing us a favour,” says Simons and I didn’t want to jeopardize their relationship with AOL any more than I already had, so at that point I pulled the plug.”

Sensing the world closing in on him a week before he was caught, Simons admits that he really should’ve asked his friends if he could start couch surfing sooner, but he just never got around to it. “Honestly, I was so busy coding and working all day long, but for about a week before I got caught I was thinking, I should really get out of here, but I was too lazy to get all of my clothes, all of the stuff, pack it up and walk two miles down the street. It was a lot more convenient just to have all my stuff at AOL.”

Sure, it was a tad unorthodox, but Simons has no regrets about making AOL his home, especially these days. After all, it was his time AOL that gave him the launch he wanted and the funding he needed. “If I came to ask for money without the AOL story, I wouldn’t seem nearly as credible as I do now,” figures Simons. “For an investor to hear that someone is willing to go broke to turn a company around, it shows that person is probably pretty capital efficient and they’re not going to walk away when and if things do go bad.”

Actually, a few investors reached out to him when they heard his story and a few are assisting with the $500,000 he is currently seeking for the next round of funding. So, would he recommend squatting in Silicon Valley as a possible option for tech entrepreneurs in need of seed capital?

“It certainly worked in my favour, but I think this is a ‘one-time use’ type thing,” says Simons. “But, I think the moral of the story is, if you go to lengths greater than the next guy to help your company succeed, you’ll probably have a pretty great story to tell investors when the time comes.”